Kid-friendly holiday rentals in Winchester

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Tiny home in Chattanooga

4.95 out of 5 average rating, 394 reviews

La Cabaña You have to climb it to get the wooness!

Pets welcome with a $35 per pet fee to a maximum of 2. Quiet mountainside tiny house on 2.5 acres in the Tennessee River Gorge will provide you with the best nights sleep. Spectacular bluff view hikes are within a few miles of the cottage. Enjoy kayaking or stand up paddle boarding along the Tennessee River with 2 rental locations within a 3 minute drive of the house. With the convenience of downtown Chattanooga only a 15 minute drive you can't miss out on everything this rental has to offer.

Top guest favourite

Home in Lookout Mountain

4.99 out of 5 average rating, 119 reviews

Dog/Family Friendly Mountain Gem near Attractions

Looking for a family and pet-friendly getaway? Look no further than The Sweet Retreat! Your cozy and comfortable vacation rental is located just off Scenic Highway and close to popular attractions, including Ruby Falls, Covenant College, Rock City, and 8 miles to Chattanooga. You'll love our high-speed internet, comfortable beds, multiple TVs, stocked kitchen, fenced yard and outdoor fire pit. With so much to see and do in the area, you'll love making The Sweet Retreat your home away from home.

Top guest favourite

Cottage in Tullahoma

4.98 out of 5 average rating, 111 reviews

Cottage at The Reserve sleeps 10

Perfect family friendly get-away at Tims Ford Lake. The cottage is located on a beautiful, completely wooded lot. You have access to Holiday Landing Marina via a subdivision golf cart path. Whether you want to go boating on the lake, hike at the nearby Tims Ford State Park, or just get together with family and friends, look no further! This large open concept, cozy, spacious, 3-level home is all you will need. Brand new furnishings and mattresses! Our space also includes 5 large 4K ROKU TVs.

Top guest favourite

Home in Lookout Mountain

4.96 out of 5 average rating, 142 reviews

Open concept, peaceful porches, quiet, clean !

Quiet, wooded, peaceful, spacious home on Lookout Mountain. Open concept floor plan with full laundry. Fully furnished kitchen for those that like to cook with a large refrigerator and dishwasher as well as an island with extra seating. Each bedroom has at least one large bed and TV. Large screen TV in family room.All TV's include Netflix.There is an outdoor basketball hoop, grill and lots of parking. Chattanooga is only 10-12 miles away. Near hiking, hang gliding, rock climbing and Rock City.

Guest favourite

Home in Tracy City

4.96 out of 5 average rating, 103 reviews

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

New 2 bedroom cabin in the Water's Edge community. Spacious family room to enjoy fireplace, TV, and dining area. Private hot tub! Master bedroom has a king sized bed. The second bedroom has 2 twin bunk beds, trundle, and a loft. Outdoor living space patio with a grill, table, couch, and firepit. Multi video game system. There is a community lake, playground, and hiking trail. We have two stand-up paddle boards, 1 adult kayak, and 1 child kayak. Pack n' play and high chair available.

Guest favourite

Cabin in Tracy City

4.95 out of 5 average rating, 118 reviews

Calming Cabin — Peaceful…Private…Caverns Near By

Park-Like, Relaxing Setting | Convenient to Hikes, Waterfalls, and The Caverns • Comfy — Full-Size Log Cabin • Front Porch Swing • Fire-pit, Picnic Table & Gas Grill • Convenient Amenities • 1GB Internet/WiFi • Full Kitchen, Ready to Cook • Loft Space w/Cozy Queen Futon • Spacious Yard • Hiking, Waterfalls, Rock Climbing—Close By • 7 min. Drive From Interstate • 15 min. from The Caverns & Sewanee Uni • Private Parking; Room for RV/Hauler • Small-Town Friendliness & Dining Close By

Guest favourite

Home in Lookout Valley

4.91 out of 5 average rating, 286 reviews

Star Cottage 1

Cute cottage at the foot of Lookout Mountain. Five miles to downtown Chattanooga and close to popular attractions. There are hiking and biking trails nearby and an easily accessible boat ramp at TVA. You will be just minutes from the freeway and there is a Walmart and restaurants just down the road. Family and pet friendly. Stocked with most of everything you will need for a great vacation! *Please pre-approve pets. We like to know the breed and that they are fully house trained.

Guest favourite

Cottage in Lookout Valley

4.92 out of 5 average rating, 149 reviews

Star Cottage 4

Beautiful 2-bedroom cottage located in Lookout Valley, TN. Please make sure you read the house rules! Located 10-15 minutes from downtown chattanooga and conveniently located 2 miles from I-24 ramp. We have a $30 dollar pet fee per stay for 2 pets additional pets will be more, so please keep that in mind when booking. All you have to do is select that you are bringing pets, and it will automatically be added to your booking. *Pets should not be left unattended in the yard!

Superhost

Cabin in Winchester

4.82 out of 5 average rating, 157 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

Guest favourite

Tiny home in Lookout Mountain

4.94 out of 5 average rating, 598 reviews

Lil' Haven at Tiny Bluff

Perched high on the brow on Lookout Mountain, our pet-friendly tiny house is packed with luxurious features and is surprisingly spacious. Lil' Haven is the perfect place to get away after a day in Chattanooga or a hike on the mountain. It’s a short drive down or along the mountain to best restaurants and state parks. Enjoy a meal out on the deck admiring the view, relax in the soaker tub, or simply sink back into the bed and stargaze through the skylights.

Guest favourite

Cabin in Lookout Mountain

4.94 out of 5 average rating, 230 reviews

Lookout Lazy Bear Cabin

Looking for a family or group of friends get away but close to Chattanooga, Rock city and Ruby Falls?? This is a cozy cabin in the woods away from everyone but close to everything! There is plenty to do outdoors! hiking, mtn biking, rock climbing, to name a few. The cabin is totally DISINFECTED and SANITIZED after each guest leaves for your safety. Come relax at our Lazy Cabin!!

Guest favourite

Cabin in Bryant

4.91 out of 5 average rating, 206 reviews

Big Time Hill Cabin with an indoor pool, hot tub,

SUNDAY check in ALLOWED. BIG TIME HILL CABIN is located inside Paradise Pointe is gated & on a mountain at tristate corner of AL/TN/GA. Walk our HIKING TRAIL to tristate corner & be in 3 states at once. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has hot tub, WIFI, fireplace, charcoal grill & fire pit!